The Offshore Sailing School Team
The photo above is a recent photo of Offshore Sailing School headquarters located in Ft. Myers, Florida. This is where Steve and Doris Colgate (our founders and owners) have their offices, along with the sales team and executive team handling finances, marketing, and operations. This group is just a few of Offshore Sailing School’s management team. Please see the Our Faculty page for information about those you will meet while taking a course. To contact members of the Offshore Sailing School team, please email Info@OffshoreSailing.com; call 800-221-4326, or 1-239-454-1700.
888-454-7015 or 239-454-1700
Sail@OffshoreSailing.com
Steve and Doris Colgate – Chairman (Steve), President & CEO (Doris)
The Colgates inspire all of us to give 110% to the art of teaching sailing. Their passion for delivering the best on-water education in fun settings started in 1964 when Steve Colgate founded Offshore Sailing School in New York City. On the recommendation of her then employer Yachting Magazine, Doris Colgate met Steve while taking a Learn to Sail and then Racing course at Offshore Sailing School. The rest is history. Read their complete story and the reasons for their dedication to sailing here.
Randon Finkelstein – Chief Operating Officer
Randon Finkelstein hails from Houston, Texas, where he discovered his passion for sailing at age 12 on local lakes and the Gulf of Mexico. Starting his career as an enthusiastic Instructor, Randon quickly rose through the ranks to become Director of Sailing and Boating, and then Chief Operating Officer. As a member of the prestigious US Sailing National Faculty and a certified US Sailing instructor at all levels, from Basic Keelboat through Passage Making, he is dedicated to inspiring new and experienced sailors and boaters to learn more. Randon holds multiple licenses and certifications, including a USCG 100-ton, RYA Oceanmaster, marine diesel engineering, and advanced open water diving. His extensive sailing experience has resulted in more than 30,000 nautical miles, including an Atlantic crossing from Portugal to Antigua, and sailing adventures in exotic locations such as Tahiti, Nova Scotia, The Florida Keys, Belize, Turks and Caicos, The British Virgin Islands, and more. Randon’s commitment to continuous learning, operational excellence, and fostering a love for sailing in others is evident in his impressive career and adventures.
Josh Julow – Vice President of Revenue Generation & Logistics
Josh Julow relocated to Florida in 2014 from the Midwest, trading fresh water for salt water. He grew up in the Metro-Detroit area and spent a decade in Milwaukee after attending Marquette University for Secondary Education. Growing up in the Great Lakes area, time on the water has always been a part of Josh’s life. He spent over 6 years at Offshore Sailing School, starting as a Sales and Marketing Intern before eventually shifting his focus to operations development and logistics. Having spent 2 years away from Offshore at Rice Windows and Doors as a Production Manager during the Covid pandemic, Josh was delighted to return to the sailing industry at the end of 2021, saying, “It is more enjoyable to sell people their dream lifestyle as opposed to a dream home.” When not on the water, Josh spends his free time moderating the largest ice hockey forum in the world, and taking advantage of Florida weather, playing golf and enjoying time on Florida’s many beaches.
Diana Smith – Sales Associate
When her two sons left the nest, Diana elected started sailing on Highlanders in Indianapolis, IN. In 1997 her General Motors job moved to Detroit where she raced on a C&C35, J120s and NA40s at Bayview Yacht Club – one season as skipper and seven seasons as crew chief. She has sailed “her favorite boat,” the Colgate 26, since its introduction in 1997 and has taken every course Offshore Sailing has to offer. During her four years as President of the National Women’s Sailing Association, she taught at Women’s Conferences, led Caribbean flotillas and Chesapeake schooner sailing programs. Diana joined Offshore in 2004.
Jill Harwood – Sales Associate
Jill grew up on the waters of Lake George and Saratoga Springs, NY. She has worked in Sales and Marketing for 20 years. As a recent empty nester, Jill realized that you must move yourself and your dreams to the front of your priorities. After years of selling for companies looking for financial gain, she was drawn to Offshore Sailing to be able to provide people with the opportunity to live their passions and dreams of sailing, and not put off the good stuff to focus on the daily grind and what everyone else needs from us. She often can be heard saying, “if not now, when?” Jill’s hobbies include, competitive darts, crafting, refurbishing furniture, boating and stand-up comedy.
Natalie Reynolds – Sales Associate
Natalie is a seasoned sales and marketing professional with a passion for connecting with people and delivering exceptional results. She has a deep love for travel and adventure, always seeking new experiences and cultures to broaden her horizons. When not working, you can often find her out on the water, enjoying boating and water sports, or hitting the open road on her motorcycle. At home, Natalie is happily married and shares her life with a beloved West Highland Terrier, who brings endless joy and companionship. With a zest for life and a love for exploration, Natalie strives to find balance between her professional pursuits and passions for travel, outdoor activities, and spending quality time with her family.
